반응 #1278144

반응 방정식

4-cyanothiophenol

3,3-dimethylcyclohexyl tosylate

potassium carbonate

→

desired intermediate

4-[(3,3-Dimethylcyclohexyl)thio]-benzonitrile

용매

DMF

EtOAc

반응 조건

후처리

1. 1
   세척wash sequentially with water (3×50 mL), saturated aqueous NaHCO3 (50 mL) and brine (50 mL)
2. 2
   건조Dry the organic phase over MgSO4
3. 3
   여과filter
4. 4
   농축concentrate in vacuo
5. 5
   기타Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1)

실험 절차

To a solution of 4-cyanothiophenol (1 g, 7.4 mmol) in DMF (15 mL) add 3,3-dimethylcyclohexyl tosylate (2.06 g, 7.4 mmol) and potassium carbonate (3.06 g, 22.2 mmol), and warm to 60° C. for 18 h. Dilute the mixture with EtOAc (50 mL) and wash sequentially with water (3×50 mL), saturated aqueous NaHCO3 (50 mL) and brine (50 mL). Dry the organic phase over MgSO4, filter and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane/EtOAc (9:1) to obtain the desired intermediate as a clear oil that solidifies on standing (0.35 g, 20%).

출처